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When you think of tech brands designed to improve our working lives, you probably picture whimsical illustrations of delighted people getting things done. Those warm and welcoming line drawings have become such a part of the digital landscape that we may not even think to ask: Why use an art form invented by cavemen to represent the most modern technology on the planet?

“So many tech companies are focused on productivity, which boils down to work—and work isn’t always fun,” says Russell Shaw, art director and illustrator at Slack. “We’re trying to remind people that, yes, this is about work, but it should also be fun. Illustration is also a great alternative to yet another stock photo of someone staring at their phone—a good a way to humanize a concept while also making it feel new.”

For Dropbox, which today announced a complete redesign emphasizing color contrasts—think purple letters on a salmon background—the link to illustration is embedded in the company’s history. “When Dropbox was brand new, the idea of cloud storage didn’t exist,” says illustration lead Michael Jeter. “The product was very buggy, and the company discovered that users were along for the ride out of loyalty to the people who made the product, more than the product itself. We did anything we could to make people smile, to make them feel like there’s some humanity behind what we’re doing. And it’s a tradition that’s carried on today.”

Images courtesy of Dropbox.

As Jeter points out, cloud storage is a commodity: Users can quickly migrate to Box, Google, and a dozen other competitors, and it’s hard to forge a brand connection with an empty square on a computer screen. When it comes to tech, most users will stick with the first product they truly understand—yet another reason to put illustration front and center.

“If you want to exaggerate the benefits of a product, and drive home how powerful a tool is, that’s something that illustration is really good at,” says Meg Robichaud, illustration lead at Shopify, a Canadian company that allows entrepreneurs to set up digital storefronts. “At the end of the day, illustration is just another communication tool, but it’s a great way to persuade people to love the weird little thing that your product does, while explaining it at the same time.”

It’s also an effective way to unify a brand across multiple realms, from product to website to blog and beyond. But if you’ve got a team of illustrators tackling dozens of assignments, it’s difficult to keep things standardized. When Shopify moved away from predictable icons to metaphorical illustrations of business owners going about their day, the new style introduced a lot more variability, and some headaches, too.

“When I first came to Shopify, I was excited about making this beautifully-neurotic style guide, but as I started seeing all the different ways that everyone draws noses and ears, I realized there’s no way to make a guide that’s detailed enough to capture it all,” says Robichaud. In the end, the four illustrators agreed on some fundamentals, like the thickness of a line stroke, folds and shadows on clothing, and the details on hands and feet. But ultimately, they were more focused on the tone of each illustration—when characters should convey a positive, neutral, or negative attitude—which would naturally vary with each situation.

Images courtesy of Shopify.

In a similar way, Dropbox created custom brushes, line weights, and color palettes for consistency, while leaving the door open enough for each artist to express their personality in their concepts. As the product’s users have gotten increasingly savvy, Dropbox has moved away from literal icons that represent folders and speech bubbles that denote comments. Now, a roped-off club says “access denied” without the need for words, and a pair of fishbowls represent storage options—clever metaphors that make users stop and think, and even smile.

“The design world has really fetishized the idea of everything being extremely simple and ‘gettable’ for everyone, and at Dropbox, we’ve got no loyalty to that,” says Jeter. “If you go on a date with someone and they immediately tell you everything about themselves, you’re just not that interested, but if you have to figure them out on your own, you start to connect with them. When we use Easter eggs and inside jokes, there’s a chance not everyone will get them, but the people who do get them suddenly have a much more human connection to our brand.”

“I think it was Michael Bierut who pointed out that as consumers get more and more informed, they’re less interested in meaning that is handed to them in a very on-the-nose way,” says Slack’s Shaw.” They really enjoy looking at something that is a little bit abstract, and then filling in the gaps; rather than saying, ‘Here’s the data’ without any emotional connection, we’re reinforcing a sense of storytelling and play.”

Illustrations from Slack.

As illustration and UX grow more sophisticated, everyone’s looking for ways to quantify impact: Robichaud is starting to plot out A/B testing options to back up her long-held hypothesis that illustration is the best way to move frustrated users to a solution. Dropbox lore has it that the aforementioned fishbowl illustrations kept thousands of users from abandoning the company’s paid plan, generating as much as a million dollars and solidifying the brand’s commitment to the art form. But Jeter is convinced there’s still plenty of room for evolution.

“Now that illustration has been co-opted as a tool in tech, everyone’s gone to this childlike, friendly style where characters are smiling at you like the Stepford Wives,” he says. “But [there’s a disconnect between] product engineers making these sophisticated tools that are incredibly nuanced while communications teams are dumbing down the messaging, as if they’re talking to two-year olds. As the industry grows up, I think we’ll find illustration styles that are even more sophisticated, but that can still help people connect to the brand. Ultimately, illustration can help you understand that the company as a whole is thinking about every little detail of the product—it shows they really want to make the best possible thing for their users.”

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Scott Kirkwood

Scott Kirkwood is a freelance copywriter and creative director in Denver, with a focus on nonprofits and “do gooder” brands. His editorial work has appeared in Communication Arts, Eye on Design, HOW, and Modern in Denver.

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